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[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R)-2-[(5R,10S,13R,14R,16R,17R)-16-acetyloxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID c8ee1934-2a25-4f95-8115-5da999587ee5
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name [(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R)-2-[(5R,10S,13R,14R,16R,17R)-16-acetyloxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoate
SMILES (Canonical) CC(C)C(=C)CCC(C1C(CC2(C1(CCC3=C2CCC4C3(CCC(=O)C4(C)C)C)C)C)OC(=O)C)C(=O)OC5C(C(C(C(O5)CO)O)O)O
SMILES (Isomeric) CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CCC(=O)C4(C)C)C)C)C)OC(=O)C)C(=O)OC5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
InChI InChI=1S/C39H60O10/c1-20(2)21(3)10-11-23(34(46)49-35-33(45)32(44)31(43)27(19-40)48-35)30-26(47-22(4)41)18-39(9)25-12-13-28-36(5,6)29(42)15-16-37(28,7)24(25)14-17-38(30,39)8/h20,23,26-28,30-33,35,40,43-45H,3,10-19H2,1-2,4-9H3/t23-,26-,27-,28+,30+,31-,32+,33-,35?,37-,38-,39+/m1/s1
InChI Key RSBAXXTZWHYISF-HYOMDHRKSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C39H60O10
Molecular Weight 688.90 g/mol
Exact Mass 688.41864811 g/mol
Topological Polar Surface Area (TPSA) 160.00 Ų
XlogP 5.10
Atomic LogP (AlogP) 4.80
H-Bond Acceptor 10
H-Bond Donor 4
Rotatable Bonds 9

Synonyms

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[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R)-2-[(5R,10S,13R,14R,16R,17R)-16-acetyloxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoate
((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl) (2R)-2-((5R,10S,13R,14R,16R,17R)-16-acetyloxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta(a)phenanthren-17-yl)-6-methyl-5-methylideneheptanoate
((3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl) (2R)-2-((5R,10S,13R,14R,16R,17R)-16-acetyloxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta(a)phenanthren-17-yl)-6-methyl-5-methylideneheptanoate
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (2R)-2-((2S,7R,11R,13R,14R,15R)-13-(acetyloxy)-2,6,6,11,15-pentamethyl-5-oxotetracyclo(8.7.0.0,.0,)heptadec-1(10)-en-14-yl)-6-methyl-5-methylideneheptanoic acid
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (2R)-2-[(2S,7R,11R,13R,14R,15R)-13-(acetyloxy)-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadec-1(10)-en-14-yl]-6-methyl-5-methylideneheptanoic acid
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R)-2-[(5R,10S,13R,14R,16R,17R)-16-acetyloxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoate
RefChem:130737
861399-71-5
CHEBI:203098

2D Structure

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2D Structure of [(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R)-2-[(5R,10S,13R,14R,16R,17R)-16-acetyloxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8455 84.55%
Caco-2 - 0.8489 84.89%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.8658 86.58%
OATP2B1 inhibitior - 0.8647 86.47%
OATP1B1 inhibitior + 0.8062 80.62%
OATP1B3 inhibitior - 0.2899 28.99%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5058 50.58%
BSEP inhibitior + 0.5828 58.28%
P-glycoprotein inhibitior + 0.7585 75.85%
P-glycoprotein substrate - 0.5741 57.41%
CYP3A4 substrate + 0.7230 72.30%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8664 86.64%
CYP3A4 inhibition - 0.7781 77.81%
CYP2C9 inhibition - 0.7544 75.44%
CYP2C19 inhibition - 0.8772 87.72%
CYP2D6 inhibition - 0.9428 94.28%
CYP1A2 inhibition - 0.7852 78.52%
CYP2C8 inhibition + 0.6433 64.33%
CYP inhibitory promiscuity - 0.8951 89.51%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.7071 70.71%
Eye corrosion - 0.9889 98.89%
Eye irritation - 0.9154 91.54%
Skin irritation + 0.5000 50.00%
Skin corrosion - 0.9390 93.90%
Ames mutagenesis - 0.5824 58.24%
Human Ether-a-go-go-Related Gene inhibition - 0.3663 36.63%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.6819 68.19%
skin sensitisation - 0.9084 90.84%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.5250 52.50%
Nephrotoxicity - 0.5885 58.85%
Acute Oral Toxicity (c) III 0.7190 71.90%
Estrogen receptor binding + 0.7474 74.74%
Androgen receptor binding + 0.7281 72.81%
Thyroid receptor binding - 0.5475 54.75%
Glucocorticoid receptor binding + 0.7328 73.28%
Aromatase binding + 0.7088 70.88%
PPAR gamma + 0.6539 65.39%
Honey bee toxicity - 0.6932 69.32%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.9915 99.15%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.27% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.86% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.72% 96.09%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 92.36% 91.24%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.47% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.93% 100.00%
CHEMBL259 P32245 Melanocortin receptor 4 87.78% 95.38%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.78% 92.62%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.11% 94.45%
CHEMBL340 P08684 Cytochrome P450 3A4 85.85% 91.19%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.59% 99.23%
CHEMBL4040 P28482 MAP kinase ERK2 85.27% 83.82%
CHEMBL221 P23219 Cyclooxygenase-1 84.74% 90.17%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.67% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.27% 86.33%
CHEMBL5255 O00206 Toll-like receptor 4 84.24% 92.50%
CHEMBL5103 Q969S8 Histone deacetylase 10 83.42% 90.08%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 83.15% 95.50%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.39% 94.00%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 82.34% 82.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.69% 99.17%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 81.57% 95.17%
CHEMBL1795139 Q8IU80 Transmembrane protease serine 6 80.38% 98.33%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 139584762
LOTUS LTS0268367
wikiData Q77375383